Lower alkyl esters of n-cyanoalkyl-n-alkyl thiolcarbamic acids as compositions



United ement o Pa ented A g: 1 35 1959 5 I was obtained 11.7 g. of n-butyl N-methyl-N-Z-cyanoethyl- 2,901,500 thiolcarba mate, n 1.4947. 1 j

The compounds of the present invention have been tested as herbicides and found very effective as the follow- TIONS 5 mg typlcal tests show. Some of the compounds are quite selective in their action and can be used to eradicate or Tllles; El and Joe Alltognilll, Mountain control one type of plant, while another type of plant is View, Cah f., assrgnors to Staulfer Chemical Company, relatively ff t d a corporatmn of Delaware In making the following tests, seeds were planted in N D i A li ti February 13, 1957 3" pots and shortly thereafter the compound under test Serial No. 639,866 was applied to the pots as a drench at the rate of 365 I pounds per acre. The pots were placed in a greenhouse 4 Clams 260-455) and watered at suitable intervals and the germination and growth of the seeds was compared with similarly planted Thls invention relates to certain novel lower alkylesters seeds to hi no herbicide was added In each case, of N-cyanoalkyl-N-alkyl thiolcarbamrc acids as herblcrdes. germination was repented on the Scale f 100%, While More specifically, the lnvention relates to compounds of growth was reported on a Scale of 040 based on the the general formula: seeds which germinated. Thus, 100-10 indicates normal 0 CHQCHQOEN germination and normal growth. The following data were obtained:

wherein R is a lower alkyl group and R is a lower alkyl Oats Cucumber Radlsh group Compound Percent Growth Percent Growth Percent Growth Preferred substituent groups are: Germ. Germ. Germ.

R1 R1 fiifiiijj: 3 33:13:33: 3 11:13:11: 3 1:11:33: R-2096 0 0 0 3-0211; n 03 7 The above tests were then repeated using application POQH rates of 10 and pounds per acre with the following results:

Rate. Pea Corn Radish Rye Cucumber Compound rhtige,

' Ge. Gr. Ge. Gr. Ge. Gr. Ge. Gr Ge. Gr.

R-2095 10 100 10 100 10 100 10 25 4 100 9 40 100 10 100 10 100 10 0 100 9 R-2096 10 100 10 100 10 100 10 15 2 7 40 100 10 100 10 100 s 0 50 7 The novel compounds of the preent invention may be The compounds of. the present invention may be used made in accordance with the following non-limiting exas preemergence or postemergence herbicides and may be amples. Code numbers have been assigned to each omapplied in a variety of ways at various concentrations. pound and are used throughout the balance of the appli- They may be combined with suitable carriers and applied cation. 50 as dusts, sprays or drenches. The amount applied will Example 1.-(R-2094).10 g. (0.080 mole) of ethyl depend on the nature of the seeds or plants to be conchlorothiolformate was dissolved in 125 cc. of ethyl ether trolled and the rate of application may vary from 1 to and the solution was cooled to 510- C. in an ice bath. 500 pounds per acre. One particularly advantageous way 13.9 g. (0.165 mole) of beta-methylaminopropionitrile of applying the compounds is as a narrow band along a was slowly added, keeping the reaction mixture cool by row p, ling the means of an ice bath. The reaction mixture was then We claim: filtered from the solid amine hydrochloride and the ether 1. The chemical compound: filtrate was concentrated on a steam bath with the aid of O CH CN CZN a current of air. There was obtained as a residue, 14 g. of u 2 2 ethyl N-methyl-N-2 cyanoethylthiolcarbamate, n 1.4971. R,

Example 2.(R2095).When the general procedure of Example 1 was repeated except that 12.4 g. (0.148 Whereln 1 18 a lower alkyl group 2 a lower y mole) of betamethylaminopropionitrile and 10 g. (0.072 grollpmole) of n-propyl chlorothiolformate were employed, 'chemlcal compound ethyl there was obtained 14 g. of npropyl N-methyl-N-Z-cyanomethyl thlolcarbamate' ethylthi o1 carbamate "D28 14954. 3. The chem1cal compound n-propyl N-cyanoethyl-N- Example 3 -(R2096) When the eneral procedure methyl thlolcarblmate' 4. The chem1cal compound n-butyl Ncyanoethyl-N- of Example 1 was repeated except that 11.3 g. (0.134 methylthiolcarbamatei mole) of betarnethyl-aminopropionitrile and 10 g. (0.066 mole) of n-butyl chlorothiolformate were employed, there (References on following page) r 3 References Cited in the file of this patent UNITED STATES PATENTS Loane et a1 June 6, 1939 Harman' Apr. 3, 1945 5 Baumgal'tner. July 24, 1951 Hook et 211. Mar. 26, 1957 

1. THE CHEMICAL COMPOUND: 